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He is married to actress Melissa Hurley and is the father of two sons, Cole Patrick and Jack Gordon.
He decided to enter his high school's drama program after breaking his collarbone while playing as the quarterback for his high school football team.
His first starring television role was in 1981 in the cautionary NBC movie Angel Dusted. In 1983, he starred in Bay City Blues as a baseball player in the minor leagues. The show was canceled after just four episodes. In 1986, he played a West Point cadet in Dress Gray (for which he received an Emmy Award nomination) and appeared in the holiday TV movie Christmas Eve with Loretta Young. He had a small but pivotal role in the Ryan O'Neal gambling opus, Fever Pitch. In 1988, he starred in the television series Dirty Dancing, based on the film. Two years later, he starred in Longtime Companion about an actor battling AIDS. In 1994, he appeared in the films I'll Do Anything and How the West Was Fun with Mary-Kate and Ashley Olsen. In 1997, he had a recurring role on TV's Lois & Clark: The New Adventures of Superman,and had another Superman-related recurring role a few years later as the biological father of Lana Lang in Smallville.
He co-starred alongside his half-brother David in a 2009 ABC Family comedy series entitled Ruby & The Rockits created by his brother Shaun. ABC Family announced on September 12, 2009 that the show had been canceled.
Cassidy's next Broadway role was Jeff Barry in the Ellie Greenwich jukebox musical Leader of the Pack. In 1990, he originated the role of The Balladeer in the original off-Broadway production of Stephen Sondheim's Assassins at Playwrights Horizons.
In 1993, Cassidy starred as Bobby opposite Carol Burnett in a Los Angeles production of Sondheim's musical Company. In 1995, he portrayed John Wilkes Booth in the Los Angeles Repertory staging of Assassins. In 1998, he was Macheath in an L.A. production of The Threepenny Opera; he was nominated for the Garland Award for Best Actor for his work in the role. In 1999, he played the title character in a national tour of Joseph and the Amazing Technicolor Dreamcoat. In 2000, Cassidy co-starred with Cheryl Ladd in Annie Get Your Gun on Broadway as Frank Butler. He later reprised his role of Frank Butler alongside Patti LuPone and George Hearn in a 2010 concert presentation at the Ravinia Festival in Illinois, directed by Lonny Price. In 2001 he played Radames in the national tour of the musical Aida; he won the 2002 National Broadway Theatre Award for Best Actor in a Touring Musical before bringing the role to Broadway in 2002. In 2004-05 he was back on Broadway in 42nd Street as Julian Marsh playing opposite his mother as Dorothy Brock.